Dicyclopentadiene → Bicyclo(2.2.1)hept-2-ene, 5-ethyl-
Reaction equation
C=CCC.[CH2:5]1[CH:9]2[CH:10]3[CH:14]=[CH:13][CH:12]([CH:8]2C=[CH:6]1)[CH2:11]3>>[CH2:5]([CH:9]1[CH2:8][CH:12]2[CH2:11][CH:10]1[CH:14]=[CH:13]2)[CH3:6]Participants
Procedure
In a 1000-ml stainless steel magnetic stirrer type autoclave in which the atmosphere had been replaced with nitrogen, 162 g of 1-butene and 198 g of dicyclopentadiene were placed, and the reaction was carried out at 170° C. for 25 hours. After the completion of the reaction, unreacted 1-butene was collected by a trap in a bath including dry ice and methanol. Afterward, the resultant reaction liquid was subjected to a vacuum distillation in order to recover 52 g of unreacted dicyclopentadiene and to obtain 97 g of 5-ethyl-2-norbornene and 8 g of a fraction of a boiling point of 87° C./1 mmHg. In this case, the amount of recovered 1-butene was 112 g. Therefore, in this Diels-Alder reaction, the conversion of 1-butene was 31% and the selectivity of 5-ethyl-2-norbornene to reacted 1-butene was 89%.
Workup
- customwas collected by a trap in a bath
- customAfterward, the resultant reaction liquid
- distillationwas subjected to a vacuum distillation in order
- customto recover 52 g of unreacted dicyclopentadiene
Sources & evidence
- ORD record
- ord-962da08e43554cfd8795473bb36abb1f
- Source dataset
- uspto-grants-1986_08
- Patent number
- US04604490
Reaction notes
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